Boron tribromide → HCID 59278189, compound

HRID 1698131Notes

Reaction equation

HRID 1698131 reaction equation
C[O:2][CH:3]1[CH2:8][CH2:7][N:6]([S:9]([C:12]2[CH:37]=[CH:36][C:15]([CH2:16][NH:17][C:18]([C:20]3[C:21]4[CH:28]=[N:27][N:26]([C:29]5[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=5)[C:22]=4[CH:23]=[N:24][CH:25]=3)=[O:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH2:5][CH2:4]1.B(Br)(Br)Br>ClCCl>[OH:2][CH:3]1[CH2:4][CH2:5][N:6]([S:9]([C:12]2[CH:13]=[CH:14][C:15]([CH2:16][NH:17][C:18]([C:20]3[C:21]4[CH:28]=[N:27][N:26]([C:29]5[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=5)[C:22]=4[CH:23]=[N:24][CH:25]=3)=[O:19])=[CH:36][CH:37]=2)(=[O:11])=[O:10])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 59278331HCID 59278331, compound

Product 1

HCID 59278189HCID 59278189, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a chilled (−78° C.) solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid 4-(4-methoxy-piperidine-1-sulfonyl)-benzylamide (0.080 g, 0.15 mmol) in dichloromethane (5 mL) was added a 1 M solution of boron tribromide (0.2 mL, 0.2 mmol) in dichloromethane. The mixture was allowed to warm to room temperature. The reaction was monitored by TLC and LC-MS indicating partial conversion. Additional boron tribromide (0.4 mL, 0.4 mmol) was added. After 30 minutes, the mixture was quenched with saturated aqueous sodium bicarbonate and was then extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine (3×5 mL), dried over magnesium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography using a gradient of 0-30% acetonitrile in EtOAc to afford the title compound as a colorless solid.

Workup

  1. customthe mixture was quenched with saturated aqueous sodium bicarbonate
  2. extractionwas then extracted with EtOAc (3×10 mL)
  3. washThe combined organic layers were washed with brine (3×5 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f6f37aa7d3ea497ca731e70a07c1cae0
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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